US3369020A - 1, 4-diformyl-2, 3, 5, 6-tetrakis(difluoramino)piperazines - Google Patents
1, 4-diformyl-2, 3, 5, 6-tetrakis(difluoramino)piperazines Download PDFInfo
- Publication number
- US3369020A US3369020A US475601A US47560165A US3369020A US 3369020 A US3369020 A US 3369020A US 475601 A US475601 A US 475601A US 47560165 A US47560165 A US 47560165A US 3369020 A US3369020 A US 3369020A
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- US
- United States
- Prior art keywords
- diformyl
- difluoramino
- parts
- tetrakis
- difluoramine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- AYLWKMMYYWNKKO-UHFFFAOYSA-N 2,3,5,6-tetrakis(difluoroamino)piperazine-1,4-dicarbaldehyde Chemical class FN(F)C1C(N(F)F)N(C=O)C(C(N(F)F)N1C=O)N(F)F AYLWKMMYYWNKKO-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 7
- -1 PIPERAZINE COMPOUND Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 17
- ULFHSQLFQYTZLS-UHFFFAOYSA-N difluoroamine Chemical compound FNF ULFHSQLFQYTZLS-UHFFFAOYSA-N 0.000 description 16
- YKZLYEKCXZMSQH-UHFFFAOYSA-N 2,3,5,6-tetrahydroxypiperazine-1,4-dicarbaldehyde Chemical compound OC1C(O)N(C=O)C(O)C(O)N1C=O YKZLYEKCXZMSQH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000001117 sulphuric acid Substances 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XZCHUMYCLYPHBG-UHFFFAOYSA-N piperazine-2,3,5,6-tetrol Chemical compound OC1NC(O)C(O)NC1O XZCHUMYCLYPHBG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S149/00—Explosive and thermic compositions or charges
- Y10S149/12—High energy fuel compounds
- Y10S149/122—Containing N, without B, P or S
Definitions
- the compound 1,4 diformyl-2,3,5,6-tetrakis(difluoramino) piperazine is prepared by reacting 1,4-diformyl-2,3,5,6- tetrahydroxy-piperazine or an ester thereof with di fluoramine in an inert atmosphere in presence of an acidic condensing agent.
- inert atmosphere is used herein to mean an atmosphere free from any constituent, such as oxygen, which reacts with difluoramine.
- reaction of the tetrahydroxy compound may be represented as follows:
- 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine used as starting material in the process of the invention may be prepared by reacting glyoxal with formamide in the presence of an alkaline catalyst as described in our copending application Ser. No. 472,717, filed July 16, 1965.
- the ester derivatives are readily prepared from the tetrahydroxy compound by esten'fying the hydroxyl groups by standard procedures.
- a convenient ester of 1,4-diformyl- 2,3,5,6-tetrahydroxypiperazine for use in the reaction is 1,4-diformyl-2,3,5,6-acetoxypiperazine.
- Convenient acidic condensing agents include halogeno sulphonic acids, concentrated sulphuric acid and oleum. Sulphuric acid is especially convenient because of its solvent action on 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine.
- 1,4-diformyl-2,3,5,G-tetrahydroxypiperazine is not entirely stable when dissolved in concentrated acid and it is therefore preferred to add the acidic condensing agent to a mixture of difluoramine and l,4-diformyl-2,3,5,6- tetrahydroxypiperazine. Using this procedure the reaction proceeds as the 1,4 diformyl 2,3,5,6 tetrahydroxypiperazine dissolves in the acidic condensing agent and the product separates from the reaction medium as a crystalline solid.
- the reaction may conveniently be carried out either under autogenous pressure at room temperature or under atmospheric pressure at a reduced temperature.
- a convenient procedure is to carry out'the reaction under conditions of difluoramine reflux at atmospheric pressure, the reflux temperature being about -23 C.
- 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine is normally used to prepare the 1,4-diformyl- 2,3,5,6-tetrakis(difluoramino)piperaz.ine
- the reaction can also be carried out using as the starting material a crude mixture of glyoxal/formamide condensation products in which diformyl-tetrahydroxypiperazine may occur to the extent of less than 50% in admixture with other condensation products.
- EXAMPLE 1 In a 3-necked-flask were placed 4.57 parts of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine which had been purified by recrystallisation from boiling water until it showed no absorption band at 6.4 in its infra-red spectrum. The flask was fitted with a reflux condenser cooled with solid carbon dioxide/ acetone, a gas inlet tube extending to the bottom of the flask and a tap-funnel for addition of sulphuric acid. A mixture of nitrogen and difluoramine was passed through the gas inlet tube until 40 parts of difluoramine had been added. The flow of nitrogen was maintained and the difluoramine allowed to reflux for 1 hour.
- C H O N F requires C, 20.8%; H, 1.73%; N, 24.3%; F, 43.9%.
- the explosion temperature of the product heated at a rate of 5 C./minute, was 202 C.
- the product burned rapidly when ignited.
- An impact sensitivity test a violent explosion was obtained when at A2 kg. mild steel hammer was dropped on to a thin layer of the product on a mild steel anvil from a height of 10 centimetres, but no explosions were obtained when the height of drop was reduced to 5 centimetres.
- EXAMPLE 2 4.66 parts crude 'diformyl-tetrahydroxypiperazine which showed a strong infrared absorption band at 6.4 11 were reacted with difluoramine in presence of sulphuric acid by the method described in Example 1. 1.79 parts of a white crystalline product melting at 162 C. were obtained. It was found to contain C, 21.1%; H, 1.9%; 9, 23.8%; F, 43.7%. The infra-red spectrum was similar to that described for the product of Example 1.
- EXAMPLE 3 6.16 parts of tetrahydroxypiperazine were reacted with 40 parts of difluoramine .in the manner described in Example 1 except that the condensing agent was 77 parts of EXAMPLE 4 6.76 parts of tetrahydroxypiperazine were reacted with 40 parts of difluoramine and the product isolated as described in Example 3 except that the condensing agent was 70 parts of fluorosulphonic acid.
- EXAMPLE 6 2.45 parts 1,4-diformyl-2,3,5,G-tetra-acetoxyperazine were reacted with 40 parts of difluoramine in presence of 55 parts sulphuric acid for 5 /2 hours by the method described in Example 1, and 1.78 parts (79% of theory) of 1,4-diformyl-2,3,5,6-tetral is(difluoramino)piperazine were isolated as described in that example. The infra-red spectrum of the product was similar to those of the products from Examples 1 and 2.
- a process for the preparation of 1,4-diformyl- 2,3,5,6-tetrakis(difluoramino-)piperazine which comprises reacting a piperazine compound selected from the group consisting of 1,4-diformyl-2,3,5,6-tetrahydroxyperazine and acetate esters thereof with difiuoramine in an inert atmosphere in presence of an acidic condensing agent.
- ester is 1,4-diformyl-2,3,5,6-acetoxypiperazine.
- the acidic condensing agent comprises a compound selected from the group consisting of halogeno sulphonic acid, concentrated sulphuric acid and oleum.
- the acidic condensing agent comprises a compound selected from the group consisting of fluorosulphonic acid and chlorosulphonic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,369,020 1,4-DIFORMYL-2,3,5,6-TETRAKIS(DIFLUOR- AMINO)PIPERAZINES Alan Norman Ferguson, Irvine, and Godfrey Fort, Ardrossan, Scotland, assignors, by mesne assignments, to the United States of America as represented by the Secretary of the Navy No Drawing. Filed July 28, 1965, Ser. No. 475,601 Claims priority, application Great Britain, Aug. 6, 1964, 32,125/ 64 7 Claims. (Cl. 260268) This invention relates to a novel compound, 1,4- diformyl-2,3,5,6-tetrakis(difluoramino)piperazine and a process for its preparation. This compound is a useful energetic constituent of high energy propellant compositions. It is especially useful in this field of application because, unlike many of the difluoramino compounds hitherto proposed, it does not show any marked tendency to sublime and it can be prepared from readily available starting materials.
In accordance with the process of the invention the compound 1,4 diformyl-2,3,5,6-tetrakis(difluoramino) piperazine is prepared by reacting 1,4-diformyl-2,3,5,6- tetrahydroxy-piperazine or an ester thereof with di fluoramine in an inert atmosphere in presence of an acidic condensing agent.
The term inert atmosphere is used herein to mean an atmosphere free from any constituent, such as oxygen, which reacts with difluoramine.
The reaction of the tetrahydroxy compound may be represented as follows:
1,4-diformyl-2,3,5,6-tetrahydroxypiperazine used as starting material in the process of the invention may be prepared by reacting glyoxal with formamide in the presence of an alkaline catalyst as described in our copending application Ser. No. 472,717, filed July 16, 1965. The ester derivatives are readily prepared from the tetrahydroxy compound by esten'fying the hydroxyl groups by standard procedures. A convenient ester of 1,4-diformyl- 2,3,5,6-tetrahydroxypiperazine for use in the reaction is 1,4-diformyl-2,3,5,6-acetoxypiperazine.
Convenient acidic condensing agents include halogeno sulphonic acids, concentrated sulphuric acid and oleum. Sulphuric acid is especially convenient because of its solvent action on 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine.
1,4-diformyl-2,3,5,G-tetrahydroxypiperazine is not entirely stable when dissolved in concentrated acid and it is therefore preferred to add the acidic condensing agent to a mixture of difluoramine and l,4-diformyl-2,3,5,6- tetrahydroxypiperazine. Using this procedure the reaction proceeds as the 1,4 diformyl 2,3,5,6 tetrahydroxypiperazine dissolves in the acidic condensing agent and the product separates from the reaction medium as a crystalline solid.
The reaction may conveniently be carried out either under autogenous pressure at room temperature or under atmospheric pressure at a reduced temperature. A convenient procedure is to carry out'the reaction under conditions of difluoramine reflux at atmospheric pressure, the reflux temperature being about -23 C.
Although purified 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine is normally used to prepare the 1,4-diformyl- 2,3,5,6-tetrakis(difluoramino)piperaz.ine, the reaction can also be carried out using as the starting material a crude mixture of glyoxal/formamide condensation products in which diformyl-tetrahydroxypiperazine may occur to the extent of less than 50% in admixture with other condensation products. I
The invention is further illustrated by the following examples in which all parts are by weight.
EXAMPLE 1 In a 3-necked-flask were placed 4.57 parts of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine which had been purified by recrystallisation from boiling water until it showed no absorption band at 6.4 in its infra-red spectrum. The flask was fitted with a reflux condenser cooled with solid carbon dioxide/ acetone, a gas inlet tube extending to the bottom of the flask and a tap-funnel for addition of sulphuric acid. A mixture of nitrogen and difluoramine was passed through the gas inlet tube until 40 parts of difluoramine had been added. The flow of nitrogen was maintained and the difluoramine allowed to reflux for 1 hour. 55 parts of 96-98% sulphuric acid were added from the tap-funnel and the mixture reacted with continuous refluxing of the difluoramine for 3 hours. The condenser temperature was allowed to rise to room temperature and unreacted difluoramine was vented off in a stream of nitrogen. The solid difluoraminated product was insoluble in the sulphuric acid and was isolated by pouring on to excess crushed ice, filtering off the product and washing thoroughly with cold water. After drying in a vacuum desiccator over phosphorus pentoxide, 5.2 parts (6 8% theory) of white, crystalline product melting at 168-170 C. were obtained. The product was found to contain C, 21.5%; H, 1.79%; N, 23.4%; F, 43.3%. Diformyl-tetrakis (difluoramino)piperazine (C H O N F requires C, 20.8%; H, 1.73%; N, 24.3%; F, 43.9%. The molecular weight, determined by an ebnllio-scopic method in acetone, was found to be 342; the calculated molecular weight for C H O N F is 346.
The product dissolved readily in acetonitrile, nitromethane and acetone. After purification by dissolving in acetone and reprecipitating with water the product melted at 171172 C.
The infra-red spectrum of a dispersion of the product in a high-boiling petroleum fraction showed strong absorption at 5.9, 8.2, 10.0 and 11.4,u, medium absorption at 7.0, 7.2, 7.65, 7.95 and 15.0,u, and weak absorption at 7.25, 10.4, 12.15 and 13.8[L- The band at 11.4;1. is characteristic of an NF linkage in a CNF group.
The explosion temperature of the product, heated at a rate of 5 C./minute, was 202 C. The product burned rapidly when ignited. In an impact sensitivity test a violent explosion was obtained when at A2 kg. mild steel hammer was dropped on to a thin layer of the product on a mild steel anvil from a height of 10 centimetres, but no explosions were obtained when the height of drop was reduced to 5 centimetres.
EXAMPLE 2 4.66 parts crude 'diformyl-tetrahydroxypiperazine which showed a strong infrared absorption band at 6.4 11 were reacted with difluoramine in presence of sulphuric acid by the method described in Example 1. 1.79 parts of a white crystalline product melting at 162 C. were obtained. It was found to contain C, 21.1%; H, 1.9%; 9, 23.8%; F, 43.7%. The infra-red spectrum was similar to that described for the product of Example 1.
EXAMPLE 3 6.16 parts of tetrahydroxypiperazine were reacted with 40 parts of difluoramine .in the manner described in Example 1 except that the condensing agent was 77 parts of EXAMPLE 4 6.76 parts of tetrahydroxypiperazine were reacted with 40 parts of difluoramine and the product isolated as described in Example 3 except that the condensing agent was 70 parts of fluorosulphonic acid.
8.90 parts of 1,4-diformyl-2,3,5,6-tetrakis(difluoramino) piperazine were obtained and identified by the infrared spectrum.
- EXAMPLE 5 6.70 parts of tetrahydroxypiperazine were reacted with 40 parts of difluoramine and the product isolated as described in Example 3 except that the condensing agent was 71 parts of chlorosulphonic acid and the period of difluoramine reflux after addition of the condensing agent was 9 hours.
5.80 parts of 1,4diformyl-2,3,5,6-tetrakis(difluoramino)piperaz.ine were obtained and identified by the infrared spectrum.
EXAMPLE 6 2.45 parts 1,4-diformyl-2,3,5,G-tetra-acetoxyperazine were reacted with 40 parts of difluoramine in presence of 55 parts sulphuric acid for 5 /2 hours by the method described in Example 1, and 1.78 parts (79% of theory) of 1,4-diformyl-2,3,5,6-tetral is(difluoramino)piperazine were isolated as described in that example. The infra-red spectrum of the product was similar to those of the products from Examples 1 and 2.
What we claim is:
1. 1,4 diformyl-2,3,5,6-tetrakis(difluoramino)piperazine.
2. A process for the preparation of 1,4-diformyl- 2,3,5,6-tetrakis(difluoramino-)piperazine which comprises reacting a piperazine compound selected from the group consisting of 1,4-diformyl-2,3,5,6-tetrahydroxyperazine and acetate esters thereof with difiuoramine in an inert atmosphere in presence of an acidic condensing agent.
3. A process as claimed in claim 2 wherein the ester is 1,4-diformyl-2,3,5,6-acetoxypiperazine.
4. A process as claimed in claim 2 wherein the acidic condensing agent comprises a compound selected from the group consisting of halogeno sulphonic acid, concentrated sulphuric acid and oleum.
5. A process as claimed in claim 4 wherein the acidic condensing agent comprises a compound selected from the group consisting of fluorosulphonic acid and chlorosulphonic acid.
6. A process as claimed in claim 2 wherein the reaction is carried out under conditions of difluoramine reflux at atmospheric pressure.
7. A process as claimed in claim 2 wherein the acidic condensing agent is added to a mixture of difluoramine and the piperazine compound.
References Cited UNITED STATES PATENTS 11/1963 Vail et a1. 260--268 OTHER REFERENCES Mitsch, J. Am. Chem. Soc., vol. 87, pp. 328 to 333, Jan. 20, 196-5.
Claims (2)
1. 1,4-DIFORMYL-2,3,5,6-TETRAKIS(DIFLUORAMINO)PIPERAZINE.
2. A PROCESS FOR THE PREPARATION OF 1,4-DIFORMYL2,3,5,6-TETRAKIS(DIFLUORAMINO)PIPERAZINE WHICH COMPRISES REACTING A PIPERAZINE COMPOUND SELECTED FROM THE GROUP CONSISTING OF 1,4-DIFORMYL-2,3,5,6-TETRAHYDROXYPERAZINE AND ACETATE ESTERS THEREOF WITH DEFLUORAMINE IN AN INERT ATMOSPHERE IN PRESENCE OF AN ACIDIC CONDENSING AGENT.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32125/64A GB1081897A (en) | 1964-08-06 | 1964-08-06 | Difluoraminated piperazine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3369020A true US3369020A (en) | 1968-02-13 |
Family
ID=10333666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US475601A Expired - Lifetime US3369020A (en) | 1964-08-06 | 1965-07-28 | 1, 4-diformyl-2, 3, 5, 6-tetrakis(difluoramino)piperazines |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3369020A (en) |
| GB (1) | GB1081897A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498711A (en) * | 1993-02-03 | 1996-03-12 | Thiokol Corporation | Synthesis of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane |
| US5529649A (en) * | 1993-02-03 | 1996-06-25 | Thiokol Corporation | Insensitive high performance explosive compositions |
| US6107483A (en) * | 1998-07-31 | 2000-08-22 | Cordant Technologies Inc. | Process for the large-scale synthesis of 4,10-dinitro-2,6,8-12-tetraoxa-4,10-diazatetracyclo-[5.5.0.05,903,11]-do decane |
| US6512113B1 (en) | 1999-06-10 | 2003-01-28 | Alliant Techsystems Inc. | Synthesis for 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]-dodecane |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112155A (en) * | 1962-02-02 | 1963-11-26 | Sidney L Vail | Glyoxal-amide reaction products |
-
1964
- 1964-08-06 GB GB32125/64A patent/GB1081897A/en not_active Expired
-
1965
- 1965-07-28 US US475601A patent/US3369020A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112155A (en) * | 1962-02-02 | 1963-11-26 | Sidney L Vail | Glyoxal-amide reaction products |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498711A (en) * | 1993-02-03 | 1996-03-12 | Thiokol Corporation | Synthesis of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane |
| US5529649A (en) * | 1993-02-03 | 1996-06-25 | Thiokol Corporation | Insensitive high performance explosive compositions |
| US6107483A (en) * | 1998-07-31 | 2000-08-22 | Cordant Technologies Inc. | Process for the large-scale synthesis of 4,10-dinitro-2,6,8-12-tetraoxa-4,10-diazatetracyclo-[5.5.0.05,903,11]-do decane |
| US6512113B1 (en) | 1999-06-10 | 2003-01-28 | Alliant Techsystems Inc. | Synthesis for 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]-dodecane |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1081897A (en) | 1967-09-06 |
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